Di-tert-butyl dicarbonate CAS 24424-99-5 in stock factory Di-tert-butyl pyrocarbonate
24424-99-5
CAS 24424-99-5
Di-tert-butyl pyrocarbonate; Dicarbonic acid bis(1,1-dimethylethyl)ester; Pyrocarbonic acid di-tert-butyl ester
tert-butoxycarbonyl anhydride
Product Name: Di-tert-butyl dicarbonate
Synonyms: (BOC)2O;(BOC)2O FLUKA;BOC;BOC ANHYDRIDE;tert-butyldicarbonate;PYROCARBONIC ACID DI-TERT-BUTYL ESTER;RARECHEM TB OC 0001;(t.-Boc)2O
CAS: 24424-99-5
MF: C10H18O5
MW: 218.25
EINECS: 246-240-1
Product Categories: Miscellaneous Reagents;Amino Acid Derivatives;Starting Raw Materials & Intermediates;Organics;N-Protecting Reagents;Biochemistry;Peptide Synthesis;Protection & Derivatization Reagents (for Synthesis);Protective Reagents (Peptide Synthesis);Reagents for Oligosaccharide Synthesis;Synthetic Organic Chemistry;Boc-Amino acid series;Pharmaceutical Intermediates;DIBOC;-
Mol File: 24424-99-5.mol
Di-tert-butyl dicarbonate Structure
Di-tert-butyl dicarbonate Chemical Properties
Melting point 23 °C(lit.)
Boiling point 65-67 °C
density 0.95 g/mL at 25 °C(lit.)
refractive index n20/D 1.409(lit.)
Fp 99 °F
storage temp. 2-8°C
form Low Melting Crystalline Solid
color White
Specific Gravity 0.950
Water Solubility Miscible with decalin, toluene, carbon tetrachloride, tetrahydrofuran, dioxane, alcohols, acetone, acetonitrile and dimethylformamide. Immiscible with water.
Sensitive Moisture Sensitive
BRN 1911173
InChIKey DYHSDKLCOJIUFX-UHFFFAOYSA-N
CAS DataBase Reference 24424-99-5(CAS DataBase Reference)
EPA Substance Registry System Dicarbonic acid, bis(1,1-dimethylethyl) ester(24424-99-5)
Safety Information
Hazard Codes T+,T,F,Xi,F+
Risk Statements 11-19-26-36/37/38-43-10-40
Safety Statements 16-26-28-36/37-45-7/9-37/39-24-36/37/39-33
RIDADR UN 2929 6.1/PG 1
WGK Germany 3
RTECS HT0230000
F 4.4-10-21
Autoignition Temperature 460 °C
Hazard Note Flammable/Irritant/Very Toxic
TSCA Yes
HazardClass 6.1
PackingGroup I
HS Code 29209010
Toxicity LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 2000 mg/kg
MSDS Information
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Di-tert-butyl dicarbonate English
SigmaAldrich English
ACROS English
ALFA English
Di-tert-butyl dicarbonate Usage And Synthesis
Chemical Properties White to off-white microcrystalline powder
Chemical Properties Di-tert-butyl dicarbonate (Boc2O) and di-tert-butyl tricarbonate ((BocO)2CO) have been used as amine carbonylating reagents to obtain linear or branched aliphatic isocyanates.
most of the known methods for transforming amines into isocyanates are not mild enough and furnish undefined products as a result of uncontrolled side reactions. However, 4-dimethylaminopyridine (DMAP)-catalyzed reaction with activated carbonates as C1 building blocks constitutes a convenient laboratory method for the phosgene-free isocyanation of amines. A procedure has been described whereby alkyl- and arylamines are converted into isocyanates in high yields by reaction with activated carbonates (for example, di-tert-butyl dicarbonate, Boc2O) in the presence of a catalytic amount of a nucleophilic nitrogen base at room temperature.
Di-tert-butyl dicarbonate (Boc2O) is a widely used reagent for introducing protecting groups in peptide synthesis. The reaction of substituted anilines with Boc2O in the presence of a stoichiometric amount of 4-dimethylaminopyridine (DMAP) in an inert solvent (acetonitrile, dichloromethane, ethyl acetate, tetrahydrofuran, toluene) at room temperature leads to aryl isocyanates in almost quantitative yields within 10 min.
Uses Reagent commonly used in organic chemistry for the introduction of the BOC protecting group.
Uses reagent for t-BOC-protected amines
Uses Reagent for the preparation of Boc-amino acids and peptides in high yields.
Purification Methods Melt the ester by heating at ~35o, and distil it in a vacuum. If IR and NMR ( 1810m 1765 cm-1 , in CCl4 1.50 singlet) suggest very max impure, then wash with an equal volume of H2O containing citric acid to make the aqueous layer slightly acidic, collect the organic layer and dry it over anhydrous MgSO4 and distil it in a vacuum. [Pope et al. Org Synth 57 45 1977, Keller et al. Org Synth 63 160 1985, Grehn et al. Angew Chem 97 519 1985.] FLAMMABLE.
Di-tert-butyl dicarbonate Preparation Products And Raw materials
Preparation Products N-Boc-D-proline-->BOC-L-Isoleucine -->5-[N-(TERT-BUTOXYCARBONYL)AMINO]-2-CHLOROPYRIDINE-->TERT-BUTYL 4-(5-FORMYL-4-METHYL-1,3-THIAZOL-2-YL)PIPERIDINE-1-CARBOXYLATE-->1-Boc-4-cyanopiperidine-->TERT-BUTYL 4-(4-FORMYL-1,3-THIAZOL-2-YL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE-->6-TERT-BUTOXYCARBONYLAMINO-PYRIDINE-2-CARBOXYLIC ACID-->1-TERT-BUTYL 6-METHYL 3-FORMYL-1H-INDOLE-1,6-DICARBOXYLATE-->(S)-N-Boc-allylglycine-->TERT-BUTYL 3-FORMYLPYRIDIN-4-YLCARBAMATE-->2-(2,2-DIMETHYL-PROPIONYLAMINO)-ISONICOTINIC ACID-->1-Boc-piperazine-->Spermidine-->TERT-BUTYL 3-(4-AMINO-2,6-DICHLOROPHENOXY)PROPYLCARBAMATE-->3-TERT-BUTOXYCARBONYLAMINO-ISONICOTINIC ACID-->6-BOC-HYDRAZINONICOTINIC ACID-->4-BOCAMINO-NICOTINIC ACID-->(S)-(-)-1-tert-Butoxycarbonyl-3-aminopyrrolidine-->(R)-PIPERAZINE-2-CARBOXYLIC ACID-->(3-HYDROXYMETHYL-PYRIDIN-4-YL)-CARBAMIC ACID TERT-BUTYL ESTER-->6-(BOC-AMINO)-HEXYL BROMIDE-->N-1-BOC-N-4-CBZ-2-PIPERAZINECARBOXYLIC ACID T-BUTYL ESTER-->4-ALLYL-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER-->1-BOC-PIPERAZINE-->TERT-BUTYL 4-(HYDROXYMETHYL)PYRIDIN-2-YLCARBAMATE-->1-BOC-4-HYDROXY-4-(HYDROXYMETHYL)-PIPERIDINE-->(S)-(-)-1-Boc-2-pyrrolidinemethanol-->TERT-BUTYL 4-FORMYL-2-METHOXYPHENYL CARB ONATE, 99-->3-[(N-(TERT-BUTYLOXYCARBONYL)AMINO)METHYL]PYRIDINE-->tert-Butyl N-(2-bromoethyl)carbamate-->N-Boc-N,N-bis(2-chloroethyl)amine-->4-CHLORO-(N-BOC)ANILINE 97-->TERT-BUTYL N-(2-HYDROXYETHYL)CARBAMATE-->4-(BOC-AMINOMETHYL)PYRIDINE-->N-BOC-piperidine-4-carboxylic acid-->1-(4-PYRIDYLMETHYL)PIPERAZINE-->N,N-DIMETHYL-2-PIPERAZIN-1-YL-ACETAMIDE-->1-Boc-3-oxopiperazine-->TERT-BUTYL 4-(METHOXYCARBONYL)PYRIDIN-2-YLCARBAMATE
Raw materials Tetrahydrofuran-->Carbon tetrachloride-->CARBON DIOXIDE-->Potassium tert-butanolate-->1,8-Diazabicyclo[5.4.0]undec-7-ene-->N-OCTANE
Name Di-tert-butyl dicarbonate
Synonyms Di-tert-butyl pyrocarbonate; Dicarbonic acid bis(1,1-dimethylethyl)ester; Pyrocarbonic acid di-tert-butyl ester
copyRight
Molecular Structure CAS # 24424-99-5, Di-tert-butyl dicarbonate, Di-tert-butyl pyrocarbonate, Dicarbonic acid bis(1,1-dimethylethyl)ester, Pyrocarbonic acid di-tert-butyl ester
Molecular Formula C10H18O5
Molecular Weight 218.25
CAS Registry Number 24424-99-5
EINECS 246-240-1
Properties
Density 0.949
Melting point 22-24 ºC
Boiling point 56-57 ºC (0.5 torr)
Refractive index 1.4075-1.4095
Flash point 37 ºC
Di-tert-butyl dicarbonate is a reagent widely used in organic synthesis. This carbonate ester reacts with amines to give N-tert-butoxycarbonyl or so-called Boc derivatives. These derivatives do not behave as amines, which allows certain subsequent transformations to occur that would have otherwise affected the amine functional group. The Boc can later be removed from the amine using acids. Thus, Boc serves as a protective group, for instance in solid phase peptide synthesis. It is unreactive to most bases and nucleophiles, allowing for an orthogonal Fluorenylmethyloxycarbonyl chloride (FMOC-Cl) protection.
Basic Info
Chemical Name tert-butoxycarbonyl anhydride
Synonyms
DBDC;
DIBOC,BOC;
Dibutyldicarbonate;
Pyrocarbonic Acid Di-tert-butyl Ester;
Di-tert-butyl Pyrocarbonate;
Expand
CAS No. 24424-99-5
Molecular Formula C10H18O5
Molecular Weight 218.24700
PSA 61.83000
LogP 2.87320
Properties
Appearance & Physical State White to off-white microcrystalline powder
Density 0.95 g/mL at 25 °C(lit.)
Boiling Point 65-67 °C
Melting Point 23 °C(lit.)
Flash Point 99 °F
Refractive Index n20/D 1.409(lit.)
Storage Condition 2-8°C
Safety Info
RTECS HT0230000
Hazard Class 6.1
Safety Statements S16; S26; S28
HS Code 29209010
Packing Group I
WGK Germany 3
RIDADR UN 2929 6.1/PG 1
Risk Statements R11; R19; R26; R36/37/38; R43; R10
Hazard Codes T+; Xi; F+
Caution Statement P210; P280; P304 + P340 + P310; P305 + P351 + P338 + P310; P370 + P378; P403 + P235
Signal Word Danger
Symbol GHS02, GHS05, GHS06
Hazard Declaration H225; H315; H317; H318; H330; H335; H336
Synthesis Route
tert-butoxycarbonyl anhydride
China
